sodium hydrogencarbonate in dimethyl sulfoxide T=100°C; 0.0833333 h;

1: SOCl2, DMF 2: 61 percent / NaBH4 / dimethylformamide; tetrahydrofuran / 3 h / Ambient temperature 3: 89 percent / pyridinium chlorochromate / CH2Cl2 / 2 h 4: 88 percent / SnCl2*2H2O, conc.HCl / 2 h / 15 °C 5: 66 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 18 h / Heating; Irradiation 6: 94 percent / silver tosylate / acetonitrile / Ambient temperature; stirred overnight 7: 26 percent / NaHCO3 / dimethylsulfoxide / 0.08 h / 100 °C View Scheme

1: 61 percent / NaBH4 / dimethylformamide; tetrahydrofuran / 3 h / Ambient temperature 2: 89 percent / pyridinium chlorochromate / CH2Cl2 / 2 h 3: 88 percent / SnCl2*2H2O, conc.HCl / 2 h / 15 °C 4: 66 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 18 h / Heating; Irradiation 5: 94 percent / silver tosylate / acetonitrile / Ambient temperature; stirred overnight 6: 26 percent / NaHCO3 / dimethylsulfoxide / 0.08 h / 100 °C View Scheme

1: 88 percent / SnCl2*2H2O, conc.HCl / 2 h / 15 °C 2: 66 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 18 h / Heating; Irradiation 3: 94 percent / silver tosylate / acetonitrile / Ambient temperature; stirred overnight 4: 26 percent / NaHCO3 / dimethylsulfoxide / 0.08 h / 100 °C View Scheme

1: 66 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 18 h / Heating; Irradiation 2: 94 percent / silver tosylate / acetonitrile / Ambient temperature; stirred overnight 3: 26 percent / NaHCO3 / dimethylsulfoxide / 0.08 h / 100 °C View Scheme

1: 89 percent / pyridinium chlorochromate / CH2Cl2 / 2 h 2: 88 percent / SnCl2*2H2O, conc.HCl / 2 h / 15 °C 3: 66 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 18 h / Heating; Irradiation 4: 94 percent / silver tosylate / acetonitrile / Ambient temperature; stirred overnight 5: 26 percent / NaHCO3 / dimethylsulfoxide / 0.08 h / 100 °C View Scheme